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Enantioselective N-Heterocyclic Carbene-Catalyzed Cascade Reaction for the Synthesis of Pyrroloquinolines via N-H Functionalization of Indoles

Abstract : Functionalization of the indole N–H bond for enantioselective synthesis of biologically important pyrroloquinoline derivatives has been reported under oxidative N-heterocyclic carbene catalysis conditions. The interception of catalytically generated chiral α,β-unsaturated acylazoliums with the indole derivatives proceeds in an aza-Michael/Michael/lactonization sequence to deliver the pyrroloquinoline derivatives in good yields, diastereoselectivities, and enantioselectivities. The simultaneous enhancement of reactivity and selectivity observed in polar aprotic solvents is noteworthy.
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02024520
Contributor : Madeleine Roux-Merlin <>
Submitted on : Tuesday, February 19, 2019 - 11:10:30 AM
Last modification on : Thursday, July 2, 2020 - 3:29:49 AM

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S. Mukherjee, S. Shee, Thomas Poisson, Tatiana Besset, A.T. Biju. Enantioselective N-Heterocyclic Carbene-Catalyzed Cascade Reaction for the Synthesis of Pyrroloquinolines via N-H Functionalization of Indoles. Organic Letters, American Chemical Society, 2018, 20 (22), pp.6998-7002. ⟨10.1021/acs.orglett.8b02820⟩. ⟨hal-02024520⟩

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